Iodine-catalyzed oxidative cyclisation for the synthesis of sarisan analogues containing 1, 3, 4-oxadiazole as insecticidal agents. Issue 96 (30th September 2016)

• Record Type: Journal Article
• Authors: Guo, Yong; Qu, Lailiang; Wang, Xiaoguang; Huang, Mengxing; Jia, Lu; Zhang, Yanbing
• Is Part Of: RSC advances. Volume 6:Issue 96(2016)
• Page Start: 93505
• Page End: 93510
• Publication Date: 2016-09-30
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c6ra22343e
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : A series of novel sarisan analogues containing 1, 3, 4-oxadiazole through iodine-catalyzed oxidative cyclisation were prepared as insecticidal agents against the pre-third Mythimna separata Walker at 1 mg mL −1 in vivo . Abstract : In continuation of our research aimed at the discovery and development of natural products-based insecticidal agents, a series of novel sarisan analogues containing 1, 3, 4-oxadiazole through iodine-catalyzed oxidative cyclisation were prepared as insecticidal agents against the pre-third Mythimna separata Walker at 1 mg mL −1 in vivo . Compound8r, 8t, 8k and8q exhibited more promising insecticidal activities with final mortality rates of >60%, when compared with sarisan and toosendanin (a commercial insecticide). An efficient way using iodine as the catalyst and K2 CO3 as base for the synthesis sarisan analogues containing 1, 3, 4-oxadiazole was developed. The results revealed that introduction of fluorophenyl or 4-cyanophenyl units on the 1, 3, 4-oxadiazole ring at the C-3 position of sarisan could afford more potent compounds. Moreover, introduction of heteroaromatic fragments on the 1, 3, 4-oxadiazole ring at the C-3 position of sarisan was very crucial for the insecticidal activity.